Tetrahydrofuran → 2-(1-Pyrrolyl)benzylamine

HRID 1161636Notes

Reaction equation

HRID 1161636 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)#[N:13]>C(O)C>[NH2:13][CH2:12][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 7073252-(1H-pyrrol-1-yl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 7073272-(1-Pyrrolyl)benzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a well stirred suspension of (0.05 mol) of lithium aluminum hydride in 100 ml of anhydrous tetrahydrofuran, (0.043 mole) of 1-(2-cyanophenyl)pyrrole were added by small portions. Then the mixture was maintained with stirring at room temperature for 18 hours. Addition of aqueous ethanol to destroy the excess lithium aluminium hydride, followed by filtration afforded a solution, which was then evaporated in vacuo. The residue was extracted with ethyl ether, the organic layer washed with water and dried over anhydrous sodium sulphate. Removal of the solvent under reduced pressure gave a crude product, which was purified by passing through an alumina column eluting with chloroform to give 1-(2-aminomethylphenyl)pyrrole.

Workup

  1. additionwere added by small portions
  2. temperatureThen the mixture was maintained
  3. stirringwith stirring at room temperature for 18 hours
  4. customto destroy the excess lithium aluminium hydride
  5. filtrationfollowed by filtration
  6. customafforded a solution, which
  7. customwas then evaporated in vacuo
  8. extractionThe residue was extracted with ethyl ether
  9. washthe organic layer washed with water
  10. dry with materialdried over anhydrous sodium sulphate
  11. customRemoval of the solvent under reduced pressure
  12. customgave a crude product, which
  13. customwas purified
  14. washeluting with chloroform

Sources & evidence

ORD record
ord-1319adc1142643c2b89c99ddaf73c99a
Source dataset
uspto-grants-2010_10
Patent number
US07820650B2

Reaction notes

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